Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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Vacation Dresses & Outfits for Effortless Getaways
Pack light and look luxe in vacay dresses and vacation outfits designed for sun-soaked escapes. Whether you’re poolside at a beach resort or exploring cobblestone streets, Windsor’s resortwear blends breezy fabrics, relaxed silhouettes, and bold prints for travel outfits you’ll want to wear on repeat.
Easy, Packable Styles
Slip into breezy maxi dresses in tropical prints or neutral tones—white, ivory, and tan—for instant cruisewear elegance. Chic rompers and vacay outfits like matching top-and-bottom sets in airy cotton or linen make packing a breeze and styling stress-free.
Day-to-Night Versatility
Transition from sunrise yoga to sunset cocktails in flowy sundresses or relaxed separates. Mix and match colorful vacation-ready separates—think high-waist shorts with off-shoulder tops—or choose effortless travel outfits in knit jumpsuits and wrap skirts that go anywhere.
Resort & Beach Essentials
Complete your look with stylish bikinis under sheer cover-up dresses or mesh tunics. Add slide sandals, statement sunglasses, and a woven tote for poolside chic. From beach days to rooftop lounges, these vacay dresses keep you feeling confident and carefree.
Ready to jet off in style? Explore Windsor’s full collection of vacation dresses and outfits online, in-app, or at your nearest Windsor store.
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Laid-Back Chic Collared Cropped Sweater
Give off a laid-back chic look for your weekend plans in this cute cropped sweater! Designed from a cozy ribbed sweater knit fabric, it features a fold-over collared neckline, a partial zip-front design, slouchy long sleeves with tapered hems, and a cropped hem. Style with the matching shorts for the perf lounge vibe!
Shop Matching Bottoms: Laid-Back Chic High Waist Shorts
Fit & Features
- Fold-over collared neckline
- Partial zip-front
- Slouchy long sleeves, tapered hems
- Cropped hem
- Ribbed sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1925
Category Name: Vacation Looks
Price: $15.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Fold-over collared neckline
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Giving Me Cozy Feels Eyelash Surplice Sweater
This cute surplice sweater will give you cozy feels! With its long sleeves and V-neckline, this top is designed for easy layering. The twisted surplice bodice adds a special touch, while the soft, eyelash knit fabric offers comfort. Complete the look in jeans and boots for a classic winter style!
Fit & Features
- Long sleeves
- V-neckline
- Surplice twisted bodice
- Cropped hem
- Soft eyelash knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1919
Category Name: Vacation Looks
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All Things Cute Cable Knit Sweater Dress
Wrap yourself up in this cute and casual cable knit sweater dress perfect for pumpkin patches or festivals! It features long sleeves with banded cuffs, a plunge surplice V-neckline and V-cut back, a tie-waist belt, and a short form-hugging fit. Complete the look in trendy knee-high boots.
Fit & Features
- Long sleeves, banded cuffs
- Plunge surplice V-neckline, V-cut back
- Tie-waist belt
- Form-hugging fit
- Short-length hem
- Cable knit design, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5370
Category Name: Vacation Looks
Price: $5.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Full Of Trendiness High-Rise Fray A-Line Maxi Skirt
Your summer is sure to be full of trendiness with this high-rise maxi skirt perfect for weekend plans! Featuring a high-rise waist and unique A-line silhouette with frayed trim, this skirt is made from soft and comfortable cotton woven fabric. Complete the look in an off-the-shoulder blouse and booties!
Fit & Features
- Cotton woven fabric, slight stretch
- High-rise waist
- Hidden side zipper and hook-eye closure
- Frayed A-Line silhouette
- Maxi-length
- Runs true to size
Style Number/Barcode: 06301-0192
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Seasonal Treat Chenille Crop Sweater
Your new go-to chenille sweater for the fall to winter months is here! It features slouchy long sleeves, ribbed cuffs and crew neck, a relaxed silhouette, and cropped hem with dual asymmetrical slit accents. Complete the look in high-rise jeans for looking at Christmas lights!
Fit & Features
- Slouchy long sleeves
- Ribbed cuffs and crew neckline
- Relaxed silhouette
- Cropped hem, asymmetrical slit accents
- Chenille knit fabric
- Soft and comfortable
- Fits true to size
Style Number/Barcode: 06005-1574
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Natural Attraction Ditsy Floral Mini Dress
You're sure to have a natural attraction to this ditsy floral mini dress - perfect for a casual birthday or afternoon tea! It features a sleeveless scoop neck, spaghetti straps, a flirty tie front, and ruched bust, and a bodycon silhouette. Style with lace-up heels for a statement finish!
Fit & Features
- Sleeveless scoop neck
- Spaghetti straps
- Tie front and ruched bust
- Bodycon silhouette
- Mini-length hem
- Ditsy floral print, smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4938
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Edge It Up Faux Leather Biker Boots
Edge up your fall 'fits with this pair of trendy faux leather biker boots. They feature an above-the-ankle height with a square toe, dual straps with buckle accents, a low block heel for comfortable wear, and are made from a smooth faux leather material. Style these biker boots with a bomber jacket and hoop earrings.
Fit & Features
- Above-the-ankle height
- Square toe
- Dual buckled straps
- Low block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1718
Category Name: Vacation Looks
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Catch Me Twirlin' Ruffle Chiffon Skater Dress
One spin and you're giving main character energy! With dreamy chiffon ruffles, sweet side cutouts, and an open back moment, this skater dress is made for sunny flings and girls’ night things.
Fit & Features
- Sheer chiffon fabric with lining
- Sleeveless sweetheart neckline, padded bra cups
- Tie-back halter straps, smocked back
- Side cutouts leading to an open lower back
- Tiered ruffled design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-000146
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Moves Criss-Cross Strap Block Heels
Make only stylish moves in these sleek strappy block heels! They feature an open square-shaped toe, thin asymmetric toe straps in a criss-cross design, thin adjustable ankle and heel straps with a buckle, and a thin block heel. Pair with an oversized blazer and a mini handbag to wear from the office to happy hour.
Fit & Features
- Open square toe
- Asymmetric criss-cross toe straps
- Adjustable ankle and heel straps, buckle detail
- Open back
- Thin block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4673
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Another Day Long Sleeve Sweater Midi Dress
Another day, another slay in this sweater midi dress - perfect for pumpkin patches, grabbing a PSL, or meeting up with friends! The knee-length dress features fitted long sleeves, a crew neckline, a bodycon silhouette, and a flirty front slit on soft and stretchy rib knit fabric. Complete the look in booties and a chic crossbody bag.
Fit & Features
- Fitted long sleeves
- Crew neckline
- Bodycon silhouette
- Front slit accent
- Midi-length hem
- Soft, stretchy sweater rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5305
Category Name: Vacation Looks
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Chic High-Rise Wrap-Slit Midi Skirt
Creating chic looks this summer with this high-rise midi skirt is essential for the weekend or casual office days. Crafted from a woven fabric with a stretchy knit lining, you'll adore this skirt all season. This skirt boasts a flattering style with delicate pleating, leading to the wrap-slit front design and a midi-length hem. Complete the look in heeled sandals and a bodysuit.
Fit & Features
- Woven fabric, stretchy knit lining
- High-rise pleated waist
- Back zipper and hook-eye closure
- Front wrap-slit design
- Midi-length
- Runs true to size
Style Number/Barcode: 06301-0187
Category Name: Vacation Looks
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendsetter Mid-Rise Belted Twill Skort
Grab a cute top and this mid-rise skort for a trendsetting outfit of the day! This skort is designed to flatter with a belted mid-rise waist and a bodycon design that accentuates your curves along the mini-length hem.
Fit & Features
- Twill woven fabric
- Mid-rise waist, adjustable belt with buckle closure
- Bodycon fit
- Mini-length hem, shorts lining
- Four-pocket styling, belt loop accents
- Front hidden hook-eye and zipper closures
- Runs true to size
Style Number/Barcode: 06303-000018
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cuddly Cute Checkered Faux Fur Bucket Hat
This cuddly cute checkered faux fur bucket hat is a trendy addition to your winter wardrobe! It features a classic bucket hat design composed of an ultra-soft faux fur material with an on-trend checkered print pattern. The woven lining features an adjustable drawstring. Style with a fringe scarf for a cozy look.
Fit & Features
- Classic bucket hat design
- Short brim
- Checkered print
- Faux fur material
- Woven lining
- Interior adjustable drawstring
Style Number/Barcode: 07302-1562
Category Name: Vacation Looks
Price: $3.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Country Nights Denim Western Booties
Go out tonight in these western booties for a country bar or bachelorette! The booties feature a pointed toe, western-inspired stitching, a stacked block heel, and a back zipper closure on an ankle-length shaft. Complete the look in a cowboy hat.
Fit & Features
- Pointed toe
- Western-inspired stitching
- Stacked block heel
- Back zipper closure
- Ankle-length shaft
- Denim material
- Runs true to size
Style Number/Barcode: 07403-1711
Category Name: Vacation Looks
Price: $4.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cue The Comfort Fuzzy Woven Fringe Scarf
You'll be ready for the cold with this fuzzy woven scarf featuring a thick and warm design to help keep you cozy and fringe details. Complete the look with a trench coat for day or night plans!
Fit & Features
- Thick fuzzy woven material
- No stretch
- Long design
- Fringe details
Style Number/Barcode: 07305-0457
Category Name: Vacation Looks
Price: $4.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Kick Up A Storm Faux Leather Western Boots
Kick up a stylish storm in these faux leather western boots! They feature a sleek pointed-toe, inner zipper closure, a block heel, trendy western-inspired stitching, and the perfect under-the-knee length with side pull tabs for easy on-and-off styling. Complete the look with a cowboy hat for a bachelorette or country concert!
Fit & Features
- Pointed-toe, block heel
- Inner zipper closure
- Western-inspired stitching
- Under-the-knee shaft length
- Side pull tabs, easy-on-and-off styling
- Faux leather material
- Runs true to size
Style Number/Barcode: 07402-0973
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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What A Cutie Knit Pom Beanie
You'll look like a total cutie in this knit beanie! Featuring a furry pom top, and a fair isle pattern, and is composed of cozy knit material. Complete the look in a puffer vest for cold days!
Fit & Features
- Furry pom top
- Fair isle pattern
- Knit material
- Warm and soft design
Style Number/Barcode: 07302-1515
Category Name: Vacation Looks
Price: $3.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stay Toasty Cable Knit Beanie
This cable knit beanie has you covered with toasty warmth and style! The cable knit fabric and foldover design make this beanie a stylish addition to any winter look. Complete the look with the matching scarf for a fun winter day!
Shop Matching Scarf: Cozy Cutie Cable Knit Fringe Scarf
Fit & Features
- Cable knit material
- Foldover design
- Soft and comfortable
Style Number/Barcode: 07302-1523
Category Name: Vacation Looks
Price: $4.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Aura Puff Sleeve Floral Lace Skater Dress
Captivate them with your flirty aura in the cutest floral lace skater dress! The dainty sheer floral lace fabric will give your look a soft feminine vibe and includes a partial woven lining for coverage. The bodice is shaped with a plunging V-neckline with a tie-front detail and sheer short puff sleeves with elasticized hems. The open back adds to the allure and features a tie-back design. The dual high waist seams lead to a fit-and-flare skater silhouette on a short-length hem that was made to twirl. Style this adorable dress with wedge heels for a spring or summer party!
Fit & Features
- Sheer floral lace fabric with partial woven lining, no stretch
- Plunging V-neckline with tie-front
- Short puff sleeves with elasticized hems
- Open back, tie-back, lower back zipper with hook and eye closure
- Dual high waist seams
- Fit-and-flare skater silhouette
- Runs true to size
Style Number/Barcode: 05101-2967
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Ready High Rise Crochet Maxi Skirt
Heading on vacation? Don't forget to grab this vacay ready high-rise crochet maxi skirt with a sultry high front slit that flaunts some leg. Pair with the matching top and your fave shades!
Fit & Features
- Crochet fabric, stretchy knit lining
- High-rise elasticized waist
- High front slit
- Flowy maxi-length silhouette
- Runs true to size
Shop The Matching Top: Vacay Ready Tie-Front Bandea Crochet Crop Top
Style Number/Barcode: 06301-0214
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Retro Vibes Belted Flared-Leg Denim Jumpsuit
This fab belted flared-leg denim jumpsuit will give off major retro vibes for the spring and summer seasons! Designed with a cotton-blend denim fabric, this jumpsuit offers plenty of stretch for comfortable wear. The sleeveless bodice is shaped with a collared V-neckline, followed by a partial zip-front design. The high-rise belted waist will create a snatched look, leading to an iconic flared-leg silhouette. Style this denim jumpsuit with platform heels.
Fit & Features
- Cotton-blend denim fabric, plenty of stretch
- Sleeveless collared V-neckline
- Zip-front
- High-rise belted waist
- Front and back pockets
- Form-hugging fit, flared-leg silhouette
- Runs true to size
Style Number/Barcode: 06602-0484
Category Name: Vacation Looks
Price: $21.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Muse Floral Satin Maxi Dress
Giving island goddess IRL. This floral satin maxi features a draped cowl neckline, crisscross back, and curve-skimming fit—perfect for destination weddings, summer soirées, or any RSVP that calls for a slay.
Fit & Features
- Floral print, satin fabric
- Cowl neckline
- Spaghetti straps
- Open strappy back tie
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000121
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute In Chevron Print Mesh Crop Top
You'll look cute in this chevron print top for festival season or hitting up the country bar! It features a sleeveless square neck, adjustable spaghetti straps, side ruched seams, and a fitted crop hem. Complete the look in the matching pants.
Shop Matching Bottoms: Cute In Chevron Print Mesh Flare Pants
Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Side ruched seams
- Fitted crop hem
- Chevron print
- Mesh fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4709
Category Name: Vacation Looks
Price: $3.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Straight To Business V-Neck Paper Bag Jumpsuit
From business to play, this paper bag jumpsuit isn't messing around when it comes to chic style! It features a sleeveless V-neck, adjustable spaghetti straps, a pleated tie-front belt waist design, hidden side pockets, and a skinny-leg silhouette on smooth woven fabric. Complete the look in this jumpsuit with a ring set and cropped blazer.
Fit & Features
- Sleeveless V-neck, adjustable spaghetti straps
- Back zipper and hook-eye closure
- Paper bag pleated waist, tie-front belt design
- Hidden side pockets
- Skinny-leg silhouette
- Smooth woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06402-1299
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale